Compounds > tri-(2-chloroisopropyl)phosphate
Page last updated: 2024-11-05

tri-(2-chloroisopropyl)phosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Tri-(2-chloroisopropyl)phosphate, also known as tris(2-chloroisopropyl) phosphate (TCIPP), is a phosphorus-containing organophosphate flame retardant that has been widely used in various applications, such as plastics, textiles, and furniture. Its synthesis involves the reaction of phosphorus oxychloride with 2-chloroisopropanol. TCIPP has been shown to exhibit flame retardant properties by interrupting the combustion process through its ability to release non-flammable gases and char formation. However, concerns have been raised about its potential adverse effects on human health and the environment. Studies have indicated that TCIPP can be toxic to aquatic organisms and may disrupt endocrine systems. It is also considered a persistent organic pollutant (POP), which means it can accumulate in the environment and pose long-term risks. Due to these concerns, the use of TCIPP has been restricted or banned in several countries. Research on TCIPP continues to focus on understanding its environmental fate, toxicity, and potential alternatives to mitigate its risks.'

Cross-References

ID SourceID
PubMed CID26176
CHEMBL ID3188873
CHEBI ID143728
SCHEMBL ID35713
MeSH IDM0196984

Synonyms (59)

Synonym
amgard tmcp
brn 1842347
einecs 237-158-7
tri-(2-chloroisopropyl)phosphate
tris(1-chloro-2-propyl)phosphate
tris(2-chloroisopropyl) phosphate
phosphoric acid, tris(2-chloro-1-methylethyl) ester
ccris 6111
hostaflam op 820
2-propanol, 1-chloro-, phosphate (3:1)
tris(2-chloroisopropyl)phosphate
13674-84-5
tris(2-chloro-1-methylethyl) phosphate
tris(1-chloropropan-2-yl) phosphate
CHEBI:143728
tris(1-chloro-2-propyl) phosphate
ec 237-158-7
tcpp phosphate cpd
hsdb 8112
2-propanol, 1-chloro-, 2,2',2''-phosphate
crt22gfy70 ,
tris(2-chloro-1-methylethyl)phosphate
unii-crt22gfy70
dtxsid5026259 ,
dtxcid106259
NCGC00257407-01
tox21_303533
cas-13674-84-5
tox21_202982
NCGC00260528-01
tcipp
phosphoric acid tris(2-chloro-1-methylethyl) ester
c9h18cl3o4p
tcpp, tris(1-chloro-2-propyl)phosphate
FT-0689156
AKOS015899872
SCHEMBL35713
Q-201899
tris(.beta.-chloroisopropyl) phosphate
tris(chloroisopropyl) phosphate
tolgard tmcp
tris(1-chloro-2-propanyl) phosphate
phosphoric acid tris(1-chloropropane-2-yl) ester
tris(1-methyl-2-chloroethyl) phosphate
levagard pp
j50.405j ,
CHEMBL3188873
mfcd00040408
98112-32-4
tris(1-chloro-2-propyl) phosphate, tech grade
tris(1-chloropropan-2-yl)phosphate
Q2454095
tris(2-chloroisopropyl)phosphate (tcpp)
tris(2-chloro-1-methylethyl) ester
flame retardant tcpp
flame retardant tris(2-chloroisopropyl)phosphate
A886642
CS-0059312
?phosphoric acid tris(2-chloro-1-methylethyl) ester

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Therefore, in this study, zebrafish embryos (2-120 h post-fertilization [hpf]) were exposed to TCIPP or TCEP (0, 100, 500 or 2500 μg/L) or a model neurotoxicant, chlorpyrifos (CPF, 100 μg/L) to investigate the adverse effects and possible mechanisms of TCIPP and TCEP on neurodevelopment."( The adverse effect of TCIPP and TCEP on neurodevelopment of zebrafish embryos/larvae.
Feng, C; Li, R; Mi, C; Wang, H; Yang, L; Zhang, L; Zhou, B, 2019)		0.51
" The aim of this study was to assess the adverse effects of TCPP exposure on the embryogenesis of the ascidian Ciona intestinalis."( Embryotoxicity characterization of the flame retardant tris(1-chloro-2-propyl)phosphate (TCPP) in the invertebrate chordate Ciona intestinalis.
Ficetola, GF; Manenti, R; Mercurio, S; Messinetti, S; Pennati, R, 2021)		0.62

Dosage Studied

ExcerptRelevanceReference
" Dermal uptake and percutaneous penetration of the OPEs were studied in a Franz diffusion cell system using human skin dosed with a mixture of OPEs in an ethanol:toluene (4:1) solution."( Dermal uptake and percutaneous penetration of organophosphate esters in a human skin ex vivo model.
Clausen, PA; Frederiksen, M; Jensen, NM; Knudsen, LE; Nielsen, F; Nielsen, JB; Stapleton, HM; Sørensen, JA; Sørensen, LS; Vorkamp, K; Webster, TF, 2018)		0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
trialkyl phosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency2.56760.006038.004119,952.5996AID1159521
GLI family zinc finger 3Homo sapiens (human)Potency12.35710.000714.592883.7951AID1259369; AID1259392
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency56.24260.001022.650876.6163AID1224839
progesterone receptorHomo sapiens (human)Potency41.70120.000417.946075.1148AID1346795
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency54.43340.001530.607315,848.9004AID1224841; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptorHomo sapiens (human)Potency61.78810.375827.485161.6524AID743220
pregnane X nuclear receptorHomo sapiens (human)Potency31.81490.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency30.70020.000229.305416,493.5996AID743080
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency0.20570.001024.504861.6448AID743215
thyroid stimulating hormone receptorHomo sapiens (human)Potency68.72910.001628.015177.1139AID1224843
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (4.17)18.2507
2000's0 (0.00)29.6817
2010's17 (70.83)24.3611
2020's6 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.41

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.41 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index5.63 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chlorpyrifos
Chlorpyrifos: An organothiophosphate cholinesterase inhibitor that is used as an insecticide and as an acaricide.. chlorpyrifos : An organic thiophosphate that is O,O-diethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.		2.2110chloropyridine;
organic thiophosphate		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
environmental contaminant;
insecticide;
xenobiotic
phencyclidine
Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.		2.1510benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug
tris(2-butoxyethyl) phosphate
tris(2-butoxyethyl) phosphate: inhibitor of drug-protein binding; present in stoppers of blood sample 'vacutainers'. tris(2-butoxyethyl) phosphate : A trialkyl phosphate in which the alkyl group specified is 2-butoxyethyl.		2.1310trialkyl phosphateenvironmental contaminant;
flame retardant
4,4'-diphenylmethane diisocyanate
4,4'-diphenylmethane diisocyanate: used as a hardening agent incorporated in polyurethanes. diphenylmethane-4,4'-diisocyanate : A diisocyanate consisting of diphenylmethane with two isocyanate groups at the 4- and 4'-positions.		2.1710diisocyanateallergen;
hapten
triphenyl phosphate
triphenyl phosphate: structure. triphenyl phosphate : An aryl phosphate resulting from the formal condensation of phosphoric acid with 3 mol eq. of phenol.		2.8330aryl phosphateflame retardant;
plasticiser
tris(chloroethyl)phosphate
tris(chloroethyl)phosphate: has gonadotoxic effects. tris(2-chloroethyl) phosphate : A trialkyl phosphate that is the tris(2-chloroethyl) ester of phosphoric acid.		2.8830organochlorine compound;
trialkyl phosphate
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.1710dialdehydebiomarker
docusate
Dioctyl Sulfosuccinic Acid: All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.		2.1110diester;
organosulfonic acid
tris(1,3-dichloro-2-propyl)phosphate
[no description available]		2.8230trialkyl phosphate
2,2',4,4'-tetrabromodiphenyl ether
[no description available]		2.1510aromatic ether;
organobromine compound
cyanates
Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).		2.1710
tris(2-carboxyethyl)phosphine
tris(2-carboxyethyl)phosphine: water-soluble reagent which irreversibly reduces disulfides to thiols at room temperature & is active below neutral pH; used for quantitation of iodine and iodate. TCEP : A tertiary phosphine in which phosphane is substituted with three 2-carboxyethyl groups. It is a commonly used reducing agent.		2.5920phosphine derivative;
tricarboxylic acid		reducing agent
trans-1-chloro-3,3,3-trifluoropropene
trans-1-chloro-3,3,3-trifluoropropene: a foam blowing and precision cleaning agent with a very low impact for global warming and ozone depletion; structure in first source		2.1710
thiosuccinic acid
thiosuccinic acid: inhibits fibrinolysin		2.1110
2-ethylhexyl 2,3,4,5-tetrabromobenzoate
2-ethylhexyl 2,3,4,5-tetrabromobenzoate: structure in first source		2.1510
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatocellular Carcinoma
[description not available]		02.4110
Innate Inflammatory Response
[description not available]		02.4110
Cancer of Liver
[description not available]		02.4110
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.4110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.4110
Liver Neoplasms
Tumors or cancer of the LIVER.		02.4110
Child Mental Disorders
[description not available]		02.2110
Neurodevelopmental Disorders
These are a group of conditions with onset in the developmental period. The disorders typically manifest early in development, often before the child enters grade school, and are characterized by developmental deficits that produce impairments of personal, social, academic, or occupational functioning. (From DSM-5).		02.2110