6974-77-2

Basic information

• Product Name: 1-Bromo-3-chloro-2-methylpropane
• Synonyms: 3-bromo-1-chloro-2-methylpropane;1-BROMO-3-CHLORO-2-METHYLPROPANE;1-CHLORO-3-BROMO-2-METHYLPROPANE;1-CHLORO-2-METHYL-3-BROMOPROPANE;Propane, 1-bromo-3-chloro-2-methyl-;1-BROMO-3-CHLORO-2-METHYLPROPANE 98%;1-Bromo-3-chloro-2-methylpropa;1-Bromo-2-methyl-3-chloropropane
• CAS NO: 6974-77-2
• Molecular Formula: C₄H₈BrCl
• Molecular Weight: 171.46
• EINECS: 230-224-6
• Product Categories: API intermediates
• Mol File: 6974-77-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 152-154 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.467 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.71mmHg at 25°C
• Refractive Index: n20/D 1.4809(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: soluble in Methanol,Acetone
• CAS DataBase Reference: 1-Bromo-3-chloro-2-methylpropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-3-chloro-2-methylpropane(6974-77-2)
• EPA Substance Registry System: 1-Bromo-3-chloro-2-methylpropane(6974-77-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 6974-77-2(Hazardous Substances Data)

Usage

Uses

1-Bromo-3-chloro-2-methylpropane is used as a reagent in the synthesis of N-substituted oxazolo[5,4-b]pyridin-2(1H)-ones as a new class of non-opiate antinociceptive agents.

InChI:InChI=1/C4H8BrCl/c1-4(2-5)3-6/h4H,2-3H2,1H3/t4-/m1/s1

Synthetic route

3-Chloro-2-methylpropene (563-47-3) → 1-bromo-3-chloro-2-methyl propane (6974-77-2)

Conditions	Yield
With hydrogen bromide; dibenzoyl peroxide
With hydrogen bromide; oxygen

isobutyryl chloride (513-36-0) → 1-bromo-3-chloro-2-methyl propane (6974-77-2)

Conditions	Yield
(i) O2, (ii) HBr; Multistep reaction;

hydrogen bromide (10035-10-6, 12258-64-9) + 3-Chloro-2-methylpropene (563-47-3) + peroxide/s → 1-bromo-3-chloro-2-methyl propane (6974-77-2)

peroxide containing 3-chloro-2-methyl-propene-(1) → 1-bromo-3-chloro-2-methyl propane (6974-77-2)

Conditions	Yield
With hydrogen bromide

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one (73942-87-7) → 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-2-methyl-3-chloro-propane (85176-88-1)

Conditions	Yield
	97.5%
With potassium tert-butylate 1.) DMSO, RT, 30 min, 2.) RT, 30 min; Multistep reaction;

1-bromo-3-chloro-2-methyl propane (6974-77-2) → 3-nitro-4-methyl-2-isoxazoline (96914-18-0)

Conditions	Yield
With n-propyl nitrite; sodium nitrite In N,N-dimethyl-formamide for 16h; Ambient temperature;	96%

2-methyl-1H-pyrroline (872-32-2) + 1-bromo-3-chloro-2-methyl propane (6974-77-2) → 2,3,5,6,7,8-hexahydro-6-methyl-1H-indolizinylium chloride

Conditions	Yield
Stage #1: 2-methyl-1H-pyrroline With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: 1-bromo-3-chloro-2-methyl propane In tetrahydrofuran; hexane at -78 - 20℃; for 15h; Stage #3: vacuo evaporation;	95%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + ethyl acetoacetate (141-97-9) → ethyl 7-chloro-6-methyl-3-oxoheptanoate (889847-91-0)

Conditions	Yield
Stage #1: ethyl acetoacetate With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1h; Stage #2: 1-bromo-3-chloro-2-methyl propane In tetrahydrofuran at -78 - 20℃; for 16h;	92%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + potassium thioacetate (10387-40-3) → thioacetic acid S-(γ-chloro-isobutyl ester) (116008-86-7)

Conditions	Yield
In acetone for 24h; Ambient temperature;	89%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + Benzhydrylamine (91-00-9) → 1-(diphenylmethyl)-3-methylazetidine hydrochloride

Conditions	Yield
Stage #1: 1-bromo-3-chloro-2-methyl propane; Benzhydrylamine With 18-crown-6 ether; sodium carbonate In water; toluene at 97℃; for 8h; Large scale; Stage #2: With hydrogenchloride In water; ethyl acetate Reagent/catalyst; Solvent; Large scale;	86.7%

1-bromo-butane (109-65-9) + 1-bromo-3-chloro-2-methyl propane (6974-77-2) → n-Butyl chloride (109-69-3) + 1,3-dibromo-2-methylpropane (28148-04-1)

Conditions	Yield
With tetrabutylammomium bromide at 105 - 110℃; Inert atmosphere; Schlenk technique;	A n/a B 86%

1-bromo-3-chloro-2-methyl propane (6974-77-2) → 1-azido-3-chloro-2-methylpropane (1202247-06-0)

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 20℃; for 20h;	84%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + N-allylbenzotriazole (52298-91-6) → 1-[1-(3-chloro)-2-methylpropenyl]-1H-1,2,3-benzotriazole (240416-54-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; Alkylation;	81%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + potassium phtalimide (1074-82-4) → 2-(3-Chloro-2-methyl-propyl)-isoindole-1,3-dione

Conditions	Yield
In chloroform-d1 for 48h; Ambient temperature;	80%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 6-methyl-2,3,4,5-tetrahydro-pyridine (1462-92-6) → 1,2,3,4,6,7,8,9-octahydro-3-methylquinolizinylium chloride

Conditions	Yield
Stage #1: 6-methyl-2,3,4,5-tetrahydro-pyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 1-bromo-3-chloro-2-methyl propane In tetrahydrofuran; hexane at -78 - 20℃; for 15h; Stage #3: vacuo evaporation;	80%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 2-hydroxybenzothiazole (934-34-9) → 3-(3-Chloro-2-methyl-propyl)-3H-benzothiazol-2-one (509148-17-8)

Conditions	Yield
With caesium carbonate In water; ethyl acetate; acetonitrile	80%
With caesium carbonate In water; ethyl acetate; acetonitrile	80%
With caesium carbonate In acetonitrile at 40℃; for 24h;	80%
With caesium carbonate In acetonitrile

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 1-(3-chlorophenyl)-2-methylpiperazine (75348-33-3) → 1-(3-chlorophenyl)-1-(3-chloro-2-methylpropyl)-3-methylpiperazine (220909-98-8)

Conditions	Yield
With sodium hydroxide In acetone 1.) RT, 48 h, 2.) 50 deg C, 1 h;	77%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + dilithium tetrachlorocuprate + propyl bromide (106-94-5) → 1-chloro-2-methylhexane

Conditions	Yield
In tetrahydrofuran	71.9%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 8-ethyl-4H-benzo[1,4]oxazin-3-one (865106-49-6) → (R,S)-4-(3-chloro-2-methylpropyl)-8-ethyl-4H-benzo[1,4]oxazin-3-one (865106-76-9)

Conditions	Yield
With caesium carbonate In ethyl acetate	69%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + thiophenol (108-98-5) → [(3-chloro-2-methylpropyl)sulfanyl]benzene (13012-61-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	69%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 3,4-dihydro-6-hydroxy-2(1H)-quinolinone (54197-66-9) → 6-(3-chloro-2-methylpropoxy)-2-oxo-1,2,3,4-tetrahydroquinoline (63309-34-2)

Conditions	Yield
With sodium ethanolate In ethanol for 12h; Heating;	68.3%

4-methyl-1-tributylstannanyl-hexan-3-one + 1-bromo-3-chloro-2-methyl propane (6974-77-2) + chloro-trimethyl-silane (75-77-4) → (Z)-9-chloro-3,8-dimethyl-4-(trimethylsiloxy)-4-nonene

Conditions	Yield
Multistep reaction;	68%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 4,6-diamino-2-mercaptopyrimidine (1004-39-3) → 8-Amino-6-imino-3-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazine-hydrobromide

Conditions	Yield
	65%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + dilithium tetrachlorocuprate + 1-bromo-3-methylheptane (5200-08-8) → 1-chloro-2,6-dimethyldecane

Conditions	Yield
With magnesium In tetrahydrofuran	62.2%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 6-amino-2-thioxo-1,2-dihydro-4(3H)-pyrimidinone (1004-40-6) → 8-amino-3,4-dihydro-3-methyl-2H,6H-pyrimido<2,1-b><1,3>thiazin-6-one (138226-22-9)

Conditions	Yield
With sodium hydroxide In isopropyl alcohol a) 1-2 h at r.t. and b) 7 h at 60 deg C;	60%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 3,4-dihydro-3-oxo-2H-1,4-benzoxazine (5466-88-6) → (R,S)-4-(3-chloro-2-methylpropyl)-4H-benzo[1,4]oxazin-3-one (560084-60-8)

Conditions	Yield
With caesium carbonate In acetonitrile	60%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + N-(m-chlorophenyl)piperazine (6640-24-0) → 1-(3-chlorophenyl)-4-(2-methyl-3-chloropropyl)piperazine (151447-87-9)

Conditions	Yield
With sodium hydroxide In acetone 1.) RT, 48 h, 2.) 50 deg C, 1 h;	57%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 1,2,3-Benzotriazole (95-14-7) → 1-(3-chloro-2-methylpropyl)-5-fuloro-1H-benzo[d]-[1,2,3]triazole (214116-69-5)

Conditions	Yield
With potassium carbonate In MeCN at 20℃; for 48h;	55%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + diethyl malonate (105-53-3) → diethyl 2-(3-chloro-2-methylpropyl)malonate (57498-82-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 80℃; for 18h;	53%
With ethanol; sodium ethanolate

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 1H-indol-4-ol (2380-94-1) → 4-(3-chloro-2-methylpropoxy)-1H-indole (873696-56-1)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h;	50%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + (2,6-dimethyl-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone → C19H27ClN2O

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃;	46%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + sodium-manganese pentacarbonyl (13859-41-1) → dimanganese decacarbonyl (10170-69-1) + eq-{(CO)5MnMn(CO)4(CCH2CH(CH3)CH2O)}

Conditions	Yield
In tetrahydrofuran under N2: dropwise addn. of a THF soln. of 10.11 mmol Na(Mn(CO)5) with stirring to 5.103 mmol 1-bromo-3-chloro-2-methylpropane; heating for 2 h at reflux; removing solvent under reduced pressure;; extraction of oil with hexane; chromy. (alumina, hexane): first band is (Mn2(CO)19), second band is MnMn-compound; recrystallization from hexane at -15°C; elem. anal.;;	A n/a B 27%

1-bromo-3-chloro-2-methyl propane (6974-77-2) → 1-chloro-2-methyl-3-nitropropane

Conditions	Yield
With sodium nitrite In dimethyl sulfoxide at 16 - 30℃; for 0.166667h; cooling;	21%

1-bromo-3-chloro-2-methyl propane (6974-77-2) + 4-oxo-2-thioxo-6-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)-1,2,3,4-tetrahydropyrimidine-5-carbonitrile → 3-methyl-6-oxo-8-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazine-7-carbonitrile

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 4h; Sealed tube;	17%

Upstream product

• 10035-10-6 hydrogen bromide 
• 563-47-3 3-Chloro-2-methylpropene 
• 513-36-0 isobutyryl chloride 

Downstream Products

• 13012-61-8 [(3-chloro-2-methylpropyl)sulfanyl]benzene 
• 109-69-3 n-Butyl chloride 
• 28148-04-1 1,3-dibromo-2-methylpropane 
• 1392724-65-0 (Z)-3-(2-isopropylphenyl)-5-methyl-2-((E)-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazono)-1,3-thiazinane 
• 1359938-02-5 N-(2-(3-benzyl-6-fluoro-2-(3-methylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide 
• 1359938-03-6 N-(2-(3-benzyl-2-(3-methylazetidin-1-yl)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide 
• 10170-69-1 dimanganese decacarbonyl 
• 151447-87-9 1-(3-chlorophenyl)-4-(2-methyl-3-chloropropyl)piperazine 
• 633317-52-9 3-(3-methyl-1-phenylcyclobutyl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine 

Relevant articles and documents

Bifunctional chelating agents

The invention related to a method of preparing a protein or a proteinaceous material labelled with a metalradionuclide and intended for diagnostic or therapeutic application, by reacting a protein or a proteinaceous material with an agent for coupling the radionuclide to the protein or the proteinaceous material, a protein conjugate being formed, and by then complexing the radionuclide with the conjugate thus formed to a radionuclide complex. A coupling agent is used which consists at least substantially of a thio compound of the general formula wherein X is a hydrogen atom or a suitable protective group, R is a branched or non-branched, optionally substituted hydrocarbon radical having 1-10 carbon atoms, which may be interrupted by one or more hereto atoms, and Y is at least one terminal reactive group capable of reacting with a functional group from the protein or the proteinaceous material; or a cyclic condensation product of the thio compound of formula I having 5-7 ring atoms, wherein X and Y together constitute a reactive group capable of reacting with a functional group from the protein or the proteinaceous material; or a water-soluble salt of this condensation product.