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Basic Information
CAS No.: 75-25-2
Name: Bromoform
Molecular Structure:
Molecular Structure of 75-25-2 (Bromoform)
Formula: CHBr3
Molecular Weight: 252.731
Synonyms: Methenyl tribromide;NSC 8019;Tribromomethane;Tribromomethane;Methyl tribromide;Tribrommethan;NCI-C55130;CCRIS 98;
EINECS: 200-854-6
Density: 2.997 g/cm3
Melting Point: 8 °C
Boiling Point: 149.2 °C at 760 mmHg
Flash Point: 44 °C
Solubility: 3.2 g/L at 30 °C in water
Appearance: colourless to yellow liquid
Hazard Symbols: ToxicT, DangerousN, FlammableF
Risk Codes: 23-36/38-51/53-22-39/23/24/25-23/24/25-11
Safety: 28-45-61-28A-36/37-16-7
Transport Information: UN 2515 6.1/PG 3
PSA: 0.00000
LogP: 2.45470
Synthetic route
941-98-0

1'-naphthacetophenone

A

75-25-2

Bromoform

B

2459-24-7

methyl 1-naphthoate

C

149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density);A n/a
B 88%
C n/a
100-06-1

1-(4-methoxyphenyl)ethanone

A

75-25-2

Bromoform

B

121-98-2

methyl 4-methoxybenzoate

C

149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density);A n/a
B 85%
C n/a
281-23-2

adamantane

75-05-8

acetonitrile

A

768-90-1

1-Adamantyl bromide

B

75-25-2

Bromoform

C

23074-42-2

1-adamantanecarbonitrile

Conditions
ConditionsYield
With carbon tetrabromide; molybdenum hexacarbonyl at 140 - 160℃; for 6h; Reactivity; Mechanism; Reagent/catalyst;A 15%
B n/a
C 85%
558-13-4

carbon tetrabromide

A

594-73-0

hexabromoethane

B

75-25-2

Bromoform

Conditions
ConditionsYield
With 2+ In water; acetonitrile at 20℃; Mechanism; Rate constant; Product distribution;A 4%
B 84%
With Co(II)W12O407-; sodium perchlorate In water; acetonitrile at 20℃; for 2h; Rate constant; Product distribution; pH 7; reaction in MeCN/D2O; reaction between CBr4 and the heteropoly blues Co(II)W12O407- and Co(II)W12O408-, kinetic and product stidy, effect of inert salts,;A 1 % Spectr.
B 77 % Spectr.
122-00-9

para-methylacetophenone

A

99-75-2

4-methyl-benzoic acid methyl ester

B

75-25-2

Bromoform

C

149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density);A 83%
B n/a
C n/a
98-86-2

acetophenone

A

93-58-3

benzoic acid methyl ester

B

75-25-2

Bromoform

C

149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With methanol; sodium bromide at 30℃; for 4h; Product distribution; Mechanism; electrolysis (Pt-anode, Cu-Zn (60:40) cathode, 220 mA/cm2 constant current); other electrolyte, other electrolyte-to-substrate ratio, other material of electrodes;A 74%
B n/a
C 15%
With methanol; sodium bromide at 30℃; for 4h; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density);A 74%
B n/a
C n/a
592-41-6

1-hexene

558-13-4

carbon tetrabromide

A

75-25-2

Bromoform

B

3740-44-1

1,1,1,3-tetrabromoheptane

C

90278-16-3

1,1,3-tribromoheptane

D

5,7,7,9-tetrabromotridecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 80℃; for 4h; Product distribution; further reagent, further conditions;A 3.7%
B 70%
C 10.1%
D 9.1%
With 2,2'-azobis(isobutyronitrile) at 80℃; for 4h;A 3.7%
B 70%
C 10.1%
D 9.1%
29949-72-2

di(tert-butyl)(n-butyl)phosphine

A

75-25-2

Bromoform

B

81193-50-2

butyl-di-t-butylchlorophosphonium bromide

Conditions
ConditionsYield
With carbon tetrabromide; hydrogen chloride In diethyl ether 1) -120 deg C to -50 deg C 2) 0 deg C, Et2O;A 70%
B 70%
563-80-4

3-methyl-butan-2-one

A

75-25-2

Bromoform

B

547-63-7

Methyl isobutyrate

C

149-73-5

trimethyl orthoformate

Conditions
ConditionsYield
With methanol; sodium bromide at 30℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm2 constant current density);A n/a
B 67%
C n/a
106053-65-0

4,5-Dimethoxy-2-(2-phenylethyl)acetophenon

A

75-25-2

Bromoform

B

106053-67-2

2-Brom-4,5-dimethoxybibenzyl

C

106053-50-3

4,5-Dimethoxy-2-(2-phenylethyl)benzoesaeure

Conditions
ConditionsYield
With sodium hydroxide; bromine In 1,4-dioxane for 1h; Ambient temperature;A n/a
B 2%
C 65%
With sodium hydroxide; bromine In 1,4-dioxane for 1h; Ambient temperature;A n/a
B 2%
C 65%
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Standards and Recommendations

OSHA PEL: TWA 0.5 ppm (skin)
ACGIH TLV: TWA 0.5 ppm (skin); Animal Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Analytical Methods

For occupational chemical analysis use NIOSH: Hydrocarbons, Halogenated, 1003.

Specification

The Bromoform with CAS registry number of 75-25-2 is also known as Methane, tribromo-. The IUPAC name and product name are the same. It belongs to product categories of Pharmaceutical Intermediates; Organics; Heterocyclic Compounds; Analytical Chemistry; Solvents for HPLC & Spectrophotometry; Solvents for Spectrophotometry; Standard Solution of Volatile Organic Compounds for Water & Soil Analysis; Standard Solutions (VOC); 600 Series Wastewater Methods; A-BAlphabetic; Alpha Sort; B; BI - BZChemical Class; BromoEPA; Halogenated; Method 601; Volatiles/ Semivolatiles. Its EINECS registry number is 200-854-6. In addition, the formula is CHBr3 and the molecular weight is 252.73.

Physical properties about Bromoform are: (1)ACD/LogP: 2.29; (2)ACD/LogD (pH 5.5): 2.29; (3)ACD/LogD (pH 7.4): 2.29; (4)ACD/BCF (pH 5.5): 32.39; (5)ACD/BCF (pH 7.4): 32.39; (6)ACD/KOC (pH 5.5): 419.56; (7)ACD/KOC (pH 7.4): 419.56; (8)Index of Refraction: 1.619; (9)Molar Refractivity: 29.83 cm3; (10)Molar Volume: 84.9 cm3; (11)Surface Tension: 49.8 dyne/cm; (12)Density: 2.974 g/cm3; (13)Flash Point: 44 °C; (14)Enthalpy of Vaporization: 39.66 kJ/mol; (15)Boiling Point: 149.2 °C at 760 mmHg; (16)Vapour Pressure: 5.17 mmHg at 25 °C.

Preparation of Bromoform: it is prepared by reaction of acetone with sodium hypobromite under alkaline conditions. Then product is derived after decomposition, distillation, washing, filtration and drying.

Bromoform is prepared by reaction of acetone with sodium hypobromite under alkaline conditions.

Uses of Bromoform: it is used to produce 1,1-dibromo-2-phenyl-cyclopropane by reaction with vinylbenzene. The reaction occurs with reagent potassium tert-butoxide and solvent pentane at ambient temperature for 10 hours. The yield is about 65%. This cehmical is also can be used as dye intermediate, disinfectant, analgesic, anesthetic, refrigerant, mineral agent, precipitating agent, solvent and liquid component of  blast-resistant.

Bromoform is used to produce 1,1-dibromo-2-phenyl-cyclopropane by reaction with vinylbenzene.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes and skin. It's toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. What's more, it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing and gloves. Avoid release to the environment. In case of accident or if you feel unwell seek medical advice immediately. After using it, keep container tightly closed  and away from sources of ignition. After contact with skin, wash immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C(Br)(Br)Br
2. InChI: InChI=1S/CHBr3/c2-1(3)4/h1H
3. InChIKey: DIKBFYAXUHHXCS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human LDLo oral 143mg/kg (143mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 141, 1969.
mammal (species unspecified) LC50 inhalation 12100mg/m3 (12100mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(4), Pg. 55, 1974.
mouse LD50 intraperitoneal 1274mg/kg (1274mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(12), Pg. 52, 1976.
mouse LD50 oral 1072mg/kg (1072mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA National Toxicology Program Technical Report Series. Vol. NTP-TR-350, Pg. 1989,
mouse LD50 subcutaneous 1820mg/kg (1820mg/kg)   Toxicology and Applied Pharmacology. Vol. 4, Pg. 354, 1962.
rabbit LDLo subcutaneous 410mg/kg (410mg/kg)   Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 28, Pg. 201, 1891.
rat LCLo inhalation 45gm/m3/4H (45000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 28, 1982.
rat LD50 intraperitoneal 414mg/kg (414mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ANTIPSYCHOTIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology Letters. Vol. 15, Pg. 251, 1983.
rat LD50 oral 933mg/kg (933mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA National Toxicology Program Technical Report Series. Vol. NTP-TR-350, Pg. 1989,

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