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2,3-ジブロモ-1-プロパノール

2,3-Dibromo-1-propanol

HCID 7281
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
96-13-9
標準SMILES
OCC(Br)CBr
InChIKey
QWVCIORZLNBIIC-UHFFFAOYSA-N
分子式
C3H6Br2O
平均分子量
217.89 g/mol
単同位体質量
215.87853901

概要

2,3-Dibromo-1-propanol can cause cancer according to The National Toxicology Program.

名称と識別子

優先名称
2,3-Dibromo-1-propanol
IUPAC
2,3-dibromopropan-1-ol
現地名
2,3-ジブロモ-1-プロパノール
英語名
2,3-Dibromo-1-propanol
分子式
C3H6Br2O
分子量
217.89

名称と別名

2,3-Dibromo-1-propanol96-13-92,3-Dibromopropan-1-ol2,3-DIBROMOPROPANOLDibromopropanol1-Propanol, 2,3-dibromo-2,3-Dibromopropyl alcoholBrominex 2571,2-Dibromopropan-3-olUSAF DO-42beta-DibromohydrinDBP (flame retardant)
名称をさらに表示
2,3-ジブロモ-1-プロパノールグリセリン-1,2-ジブロモヒドリンβ-ジブロモヒドリンα,β-ジブロモヒドリングリセロールα,β-ジブロモヒドリン2,3-ジブロモプロピルアルコールブロミネックス257アリルアルコールジブロミド2,3-ジブロモ-1-プロパノ-ル2,3ジブロモ1プロパノル[[[2,3-ジブロモ-1-プロパノール2,3-ジブロモプロパノール2,3-ジブロモプロパン-1-オール2・3-ジブロモ-1-プロパノール2,3‐ジブロモ‐1‐プロパノールusafdo-42brominex2571,2-DIBROMOHYDRINDibromo-1-propanol
NCI-C55436Allyl alcohol dibromideDTXSID7021817Glycerol 1,2-dibromohydrinC0YBW1OA2INSC-6203DTXCID801817NSC6203

データベース識別子

物性

構造計算による物性

XLogP
1.1
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
2
重原子数
6
形式電荷
0
複雑度
32

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Halogenated Alcohols

Carcinogens

SpringerMaterials PropertiesBoiling point
Density · 2 件

2.12 at 68 °F (NTP, 1992) - Denser than water; will sink

2.120 @ 20 °C/4 °C

Color/FormCOLORLESS LIQUID
Solubility · 3 件

50 to 100 mg/mL at 68 °F (NTP, 1992)

SOL IN ACETONE, ALCOHOL, ETHER, BENZENE

In water, 5.20X10+4 mg/l @ 25 °C.

Flash Point · 2 件

greater than 235 °F (NTP, 1992)

Flash point > 113 °C

Boiling Point · 2 件

426 °F at 760 mmHg (NTP, 1992)

219 °C

DecompositionWhen heated to decomposition it emits toxic fumes.
Vapor Pressure · 3 件

1 mmHg at 134.6 °F ; 5 mmHg at 184.1 °F; 10 mmHg at 208.8 °F (NTP, 1992)

0.09 [mmHg]

0.09 mm Hg @ 25 °C

Physical Description

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P316, P317, P318, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P316, P317, P318, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: 1-Propanol, 2,3-dibromo-

Hazard Traits - Carcinogenicity

Status: Active Update: 12-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24666

Substance: 2,3-dibromo-1-propanol (2,3-DBPA)

2,3-Dibromopropanol: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 1-Propanol, 2,3-dibromo-: Environment tier I assessment
DOT LabelPoison
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Hazards Summary · 1 件

A mutagen, tumorigen and severe eye irritant; Causes somnolence and dyspnea in lethal-dose inhalation studies of rats; [RTECS] A skin, eye, mucous membrane, and respiratory tract irritant; Harmful by inhalation, ingestion, and skin absorption; [CAMEO] A severe eye irritant; Readily absorbed through skin; [MSDSonline]

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

2,3-DIBROMOPROPANOL, A METABOLITE OF TRIS-BP & A MUTAGEN ITSELF, WAS FOUND IN THE URINE SAMPLES OF 10 CHILDREN WHO WERE WEARING OR WHO WORE TRIS-BP-TREATED SLEEPWEAR.

WHEN TRIS(2,3-DIBROMOPROPYL) PHOSPHATE WAS APPLIED TO THE SKIN OF A RAT, ITS HYDROLYSIS PRODUCT, 2,3-DIBROMOPROPANOL, WAS DETECTED IN THE URINE.

用途と製造

Uses · 3 件

Used to make flame retardants, insecticides, and pharmaceuticals; [HSDB]

Intermediate in the preparation of flame retardants, insecticides, and pharmaceuticals.

Main use is in the production of tris(1,2,3-dibromopropyl) phosphate, commonly called Tris.

U.S. Production · 2 件

(1972) PROBABLY GREATER THAN 9.08X10+5 GRAMS

(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS

Methods of ManufacturingREACTION OF ALLYL ALCOHOL WITH BROMINE IN CARBON TETRACHLORIDE
Household ProductsCosmetics product ingredient: 2,3-Dibromo-1-propanol
General Manufacturing Information1-Propanol, 2,3-dibromo-: ACTIVE
応用分野 · 3 件

用途有機合成原料(医薬?農薬?電材?工業用等),難燃剤中間体

使用2,3-Dibromo-1-propanol is a metabolite of the flame retardant tris(2,3-dibromopropyl) phosphate (T775560), previously shown to be a mutagen and carcinogen in experimental animals.

一般的な説明Clear colorless to slightly yellow viscous liquid.

調製方法

関連反応

6 件
反応記録を作成
HRID 579821 の反応式
HRID 579821反応物としてuspto-grants-1988_06
HRID 579823 の反応式
HRID 579823反応物としてuspto-grants-1988_06
HRID 848575 の反応式
HRID 848575反応物としてuspto-grants-1981_10
HRID 894585 の反応式
HRID 894585反応物としてuspto-grants-1981_08
HRID 1164440 の反応式
HRID 1164440反応物としてuspto-grants-1983_01
HRID 1757910 の反応式
HRID 1757910反応物としてuspto-grants-1983_02

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
CAS
96-13-9
PubChem CID
7281
DTXSID
DTXSID7021817
ChEMBL
CHEMBL1403428
UNII
C0YBW1OA2I
EC Number
202-480-9
Nikkaji
J3.961F
· 2 件

2,3-dibromo-1-propanol is a clear colorless to slightly yellow viscous liquid. (NTP, 1992)

Colorless to slightly yellow liquid; [CAMEO] Faintly yellow clear viscous liquid; [MSDSonline]

物理化学的性質

融点
9 °C · 9 °C
沸点
95 · 95-97 °C/10 mmHg (lit.)
比重(密度)
2.12 g/mL · 2.12 g/mL at 25 °C (lit.)
屈折率
20 · n20/D 1.559(lit.)
闪点
230 °F · >230 °F
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
外見
clear liquid
酸解離定数(Pka)
13.69 · 13.69±0.10(Predicted)
色
Colorless to Light yellow
水溶解度
20 ℃で5~10g/100mL · 20℃で5~10g/100mL
BRN
1719127 · 1719127
Henry's Law Constant
1.6 · 1.6×102 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C3H6Br2O/c4-1-3(5)2-6/h3,6H,1-2H2
InChIKey
QWVCIORZLNBIIC-UHFFFAOYSA-N
SMILES
OCC(Br)CBr
CAS データベース
96 · 96-13-9(CAS DataBase Reference)
NISTの化学物質情報
1 · 1-Propanol, 2,3-dibromo-(96-13-9)
EPAの化学物質情報
2 · 2,3-Dibromopropanol (96-13-9)

化学的性質

化学的特性2,3-Dibromo-1-propanol is a clear, colorless to slightly yellow thick liquid.

Reactive GroupAlcohols and Polyols
Special Reports · 2 件

DHHS/NTP; Toxicology & Carcinogenesis Studies of 2,3-Dibromo-1-propanol in F344/N Rats and B6C3F1 Mice (Dermal Studies) Technical Report Series No. 400 (1993) NIH Publication No. 94-2855

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2,3-Dibromo-1-propanol (96-13-9) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s060dibr.pdf]

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,3-Dibromopropanol is included on this list.

Reactivity Profile2,3-DIBROMO-1-PROPANOL is incompatible with strong oxidizers. (NTP, 1992)
Air and Water ReactionsWater soluble.
Hazard Classes and Categories · 6 件

Acute Tox. 4 (100%)

Acute toxicity - category 3

Carcinogenicity - Category 1B

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Carcinogens, Mutagens

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a structure estimation method(2), indicates that 2,3-dibromopropanol is expected to have very high mobility in soil(SRC). Volatilization of 2,3-dibromopropanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-8 atm-cu m/mole(SRC), obtained using a fragment constant estimation method(3). 2,3-Dibromopropanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.09 mm Hg(4). Limited data indicate that 2,3-dibromopropanol may biodegrade under aerobic conditions(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a structure estimation method(2), indicates that 2,3-dibromopropanol is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.3X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(3,SRC), from an estimated log Kow(6,SRC), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Limited data indicate that 2,3-dibromopropanol may biodegrade under aerobic conditions(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-dibromopropanol, which has a vapor pressure of 0.092 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-dibromopropanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half- life for this reaction in air is estimated to be 8 days(SRC) from its estimated rate constant of 2.07X10-12 atm cu m/mol(3).

Adverse EffectsIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=96-13-9]

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,3-dibromopropanol can be estimated to be about 4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,3-dibromopropanol is expected to have very high mobility in soil.

Artificial Pollution Sources2,3-Dibromopropanol's production and use as a chemical intermediate for flame retardants, insecticides, and pharmaceuticals(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationCell-free extracts of Flavobacterium sp isolated from soil degraded 2,3-dibromopropanol to epibromohydrin, dihydroxybromopropane, glycidol, and ultimately glycerin(1,2).
Carcinogen Classification · 6 件

2,3-Dibromopropan-1-ol

Group 2B: Possibly carcinogenic to humans

Volume 77: (2000) Some Industrial Chemicals

2000

2000

2,3-Dibromo-1-Propanol

Environmental Bioconcentration · 1 件

An estimated BCF of 3 was calculated for 2,3-dibromopropanol(SRC), using an estimated log Kow of 0.96(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 件

The Henry's Law constant for 2,3-dibromopropanol is estimated as 6.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3-dibromopropanol is expected to be essentially nonvolatile(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 107 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 780 days(SRC). 2,3-Dibromopropanol's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 2,3-Dibromopropanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.092 mm Hg(3).

Non-Human Toxicity Excerpts · 4 件

A SINGLE IP INJECTION OF THE CARCINOGENIC FLAME RETARDANT, TRIS(2,3-DIBROMOPROPYL)PHOSPHATE (TRIS-BP) (154 MG/KG), WHEN ADMIN TO MALE SPRAGUE-DAWLEY RATS, CAUSED POLYURIC ACUTE RENAL FAILURE WITH TUBULAR NECROSIS INVOLVING THE LATE PROXIMAL TUBULE. GLOMERULAR FILTRATION RATE AND IN VITRO TRANSPORT OF THE ORGANIC ACID, PARA-AMINOHIPPURATE AND THE ORGANIC BASE, METHYLNICOTINAMIDE, WERE DEPRESSED. IN CONSTRAST, AN APPROX EQUIMOLAR DOSE OF THE METABOLITE 2,3-DIBROMOPROPANOL (BP) (61 MG/KG) WAS NONNEPHROTOXIC.

... CONCLUSIONS Under the conditions of these long term dermal studies, there was clear evidence of carcinogenic activity of 2,3-dibromo-1 -propanol in male F344/N rats based on increased incidences of neoplasms of the skin, nose, oral mucosa, esophagus, forestomach, small and large intestine, Zymbal's gland, liver, kidney, tunica vaginalis, and spleen. There was clear evidence of carcinogenic activity of 2,3-dibromo-1-propanol in female F344/N rats based on increased incidences of neoplasms of the skin, nose, oral mucosa, esophagus, forestomach, small and large intestine, Zymbal's gland, liver, kidney, clitoral gland, and mammary gland. There was clear evidence of carcinogenic activity of 2,3-dibromo-1- propanol in male B6C3F1 mice based on increased incidences of neoplasms of the skin, forestomach, liver, and lung. There was clear evidence of carcinogenic activity of 2,3-dibromo-1-propanol in female B6C3F1 mice based on increased incidences of neoplasms of the skin and the forestomach. The increased incidences of alveolar/bronchiolar adenomas in female mice may have been related to chemical administration.

2,3-Dibromo-1-propanol is a metabolite of the flame retardant tris(2,3-dibromopropyl) phosphate, previously shown to be a mutagen and carcinogen in experimental animals. Toxicology and carcinogenesis studies of 2,3-dibromo-1-propanol were conducted by applying the chemical in 95% ethanol to the interscapular skin of male and female F344/N rats and B6C3F1 mice 5 days a week for 13 weeks in the prechronic study and 48-55 weeks (rats) or 36-42 weeks (mice) in the carcinogenicity study. In the 13-week study, 10 rats and 10 mice of each sex received doses of 0, 44, 88, 177, 375, or 750 mg/kg. Deaths associated with chemical application occurred only in the high-dose (750 mg/kg) male mice. Chemical-related lesions were seen in the kidney of male rats, liver of female rats, and liver and lung of both sexes of mice. Based on the toxicity observed in the 13-week study, 50 rats of each sex received doses of 0, 188, or 375 mg/kg and 50 mice of each sex received 0, 88, or 177 mg/kg in the carcinogenicity study. The planned 2-year study was terminated early because of reduced survival of rats related to chemical-induced neoplasia and because of the appearance of antibodies to lymphocytic choriomeningitis virus in sentinel mice. Nearly all dosed rats had malignant neoplasms at one or more sites, while only one control male and one control female had malignant neoplasms. In rats, neoplasms induced by 2,3-dibromo-1-propanol occurred in the skin, nasal mucosa, Zymbal's gland, oral mucosa, esophagus, forestomach, intestines, liver, kidney, mammary gland (females), clitoral gland (females), spleen (males), and mesothelium (males). In mice, chemical-induced neoplasms occurred in the skin, forestomach, liver (males), and lung (males).

Evidence for Carcinogenicity2,3-Dibromo-1-propanol: reasonably anticipated to be a human carcinogen.
Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of 2,3-dibromopropanol with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3-Dibromopropanol is not expected to directly photolyze due to the lack of absorption in the environmental spectrum(2).

法規制情報

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,3-Dibromopropanol is included on this list.

安全データ

wgk
3
tsca
TSCA listed
rtecs
UB0175000
ridadr
UN 2810 6.1/PG 2
PRTR法
第二種指定化学物質
hs_code
29055900
risk_code
45-20/22-24-52/53-62
化審法
(2)-2002
消防法
危-4-3-III
hazard_code
T
safety_code
53-45-61
hazard_class
6.1(b)
packing_group
III
毒劇物取締法
劇物
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Carc. 1BRepr. 2
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
96-13-9(Hazardous Substances Data)

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上流・下流製品情報

上流原料

四塩化炭素臭素アリルアルコール

下流製品

1,2,3-プロパントリオール1,2-ジニトラート3-ブロモプロパン-1,2-ジオール1,4-ジトシル-1,4-ジアゼパン-6-オール

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Drosophila mutagenicity tests of 45 chemical compounds were assayed for the National Toxicology Program. Each chemical was tested blind for the induction of sex linked recessive lethals. The nine positive compounds that induced recessive lethals included 1,2-dibromo-3-chloropropane and 2,3-dibromo-1-propanol. 1,2-Dibromo-3-chloropropane was found to be strongly mutagenic.