78-99-9

Basic information

• Product Name: 1,1-Dichloropropane
• Synonyms: 1,1-Dichloropropane; 4-01-00-00195 (Beilstein Handbook Reference); BRN 1731152; HSDB 5131; Propane, 1,1-dichloro-; Propylidene chloride; R 270fb; alpha,alpha-Dichloropropane; alpha,alpha-Propylene dichloride; Propylidene dichloride
• CAS NO: 78-99-9
• Molecular Formula: C₃H₆Cl₂
• Molecular Weight: 112.99
• EINECS: 201-165-3
• Mol File: 78-99-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 88 °C(lit.)
• Flash Point: 45 °F
• Appearance: /
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 78.3mmHg at 25°C
• Refractive Index: 1.419
• CAS DataBase Reference: 1,1-Dichloropropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dichloropropane(78-99-9)
• EPA Substance Registry System: 1,1-Dichloropropane(78-99-9)

Safety Data

• Hazardous Substances Data: 78-99-9(Hazardous Substances Data)

Usage

General Description

1,1-Dichloropropane is a colorless liquid chemical compound that is primarily used as an intermediate in the production of other chemicals. It is a member of the chlorinated hydrocarbon group and is highly volatile, with a strong odor and low solubility in water. The chemical is considered hazardous and toxic, causing irritation to the eyes, skin, and respiratory system upon exposure. It is also a known carcinogen, with potential long-term health effects from prolonged or repeated exposure. Given its hazardous nature, 1,1-Dichloropropane is heavily regulated and its use is strictly limited in industrial and commercial settings.

InChI:InChI=1/C3H6Cl2/c1-2-3(4)5/h3H,2H2,1H3

Synthetic route

propane (74-98-6) → 1,1-dichloropropane (78-99-9)

Conditions	Yield
at 400℃; bei der Chlorierung;

propane (74-98-6) → 1,2-Dichloropropane (26198-63-0, 78-87-5) + 2,2-dichloropropane (594-20-7) + 1,1-dichloropropane (78-99-9) + 1,3-Dichloropropane (142-28-9)

Conditions	Yield
at 400℃; Product distribution; thermische Chlorierung;
at 400℃; Product distribution; thermische Chlorierung;

propionaldehyde (123-38-6) → 1,1-dichloropropane (78-99-9)

Conditions	Yield
With phosphorus pentachloride

propenyl chloride (590-21-6) → 1,1-dichloropropane (78-99-9)

Conditions	Yield
With hydrogenchloride; iron(III) chloride at 25℃; im Dunkeln;

bromodichloromethane (75-27-4) + ethene (74-85-1) → 1,1-dichloropropane (78-99-9)

Conditions	Yield
Irradiation;

1-Chloropropane (540-54-5) → 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,1-dichloropropane (78-99-9) + 1,3-Dichloropropane (142-28-9)

Conditions	Yield
With chlorine In 1,2-dichloro-benzene at 0℃; Product distribution; oth. temperatures;
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; Product distribution; Rate constant; Irradiation; relative rate constants, position selectivity, substrate selectivity;
With chlorine In benzene at -10.1℃; Product distribution; dependence of the selectivity of chlorination on the conc. of benzene;
With sulfuryl dichloride; dibenzoyl peroxide
With chlorine Ambient temperature; Irradiation;

propionaldehyde (123-38-6) → 1,1-dichloropropane (78-99-9) + N-chlorocarbonyl-carbonimidic acid dichloride (26551-86-0)

Conditions	Yield
With iron(III) chloride; perchloro-2-aza-1-propene

1-Chloropropane (540-54-5) → 1,1-dichloropropane (78-99-9) + 1,2-dichloro-propane and 1,3-dichloro-propane

Conditions	Yield
With chlorine at 305℃;

propane (74-98-6) + chlorine (7782-50-5) + tetraethyllead(IV) (78-00-2) → 1-Chloropropane (540-54-5) + isopropyl chloride (75-29-6) + 1,1-dichloropropane (78-99-9)

Conditions	Yield
at 136 - 140℃; Product distribution;
at 136 - 140℃; Product distribution;

propane (74-98-6) + chlorine (7782-50-5) → 1-Chloropropane (540-54-5) + 1,1-dichloropropane (78-99-9) + 1,1,1-trichloropropane (7789-89-1) + 1,1,1,2-tetrachloropropane (812-03-3)

Conditions	Yield
at 360 - 395℃;

propane (74-98-6) + chlorine (7782-50-5) + copper (II)-chloride /silicon dioxide → 1-Chloropropane (540-54-5) + 1,1-dichloropropane (78-99-9) + 1,1,1-trichloropropane (7789-89-1) + 1,1,1,2-tetrachloropropane (812-03-3)

Conditions	Yield
at 230 - 347℃;

propane (74-98-6) + chlorine (7782-50-5) + iron → 1-Chloropropane (540-54-5) + 1,1-dichloropropane (78-99-9) + 1,1,1-trichloropropane (7789-89-1) + 1,1,1,2-tetrachloropropane (812-03-3)

Conditions	Yield
at 230 - 347℃;

1-Chloropropane (540-54-5) + chlorine (7782-50-5) → 1,2-Dichloropropane (26198-63-0, 78-87-5) + 1,1-dichloropropane (78-99-9) + 1,3-Dichloropropane (142-28-9)

1,1-dichloropropane (78-99-9) + methyl 3,3-dimethyl-4-penteneoate (63721-05-1) → C11H20Cl2O2

Conditions	Yield
With diacetyl peroxide at 80℃; for 6h; Inert atmosphere; Autoclave; Green chemistry;	98.1%

1,1-dichloropropane (78-99-9) + para-bromobenzenethiol (106-53-6) → 1,1-di(4-bromophenylthio)propane

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 150℃; for 0.333333h; microwave irradiation;	95%

1,1-dichloropropane (78-99-9) + Mo(N[((t)Bu)(3,5-C6H3Me2)])3 → tris[N-(tert-butyl)(3,5-dimethylphenyl)amido]molybdenum(VI) propylidyne

Conditions	Yield
With Mg In tetrahydrofuran; pentane to soln. of Mo(N(t-Bu)(3,5-C6H3Me2))3 in THF added CH3CH2CHCl2 under Ar;mixt. stirred for 1.5 h at room temp. in presence of magnesium; solvent removed in vac. and residue redissolved in pentane; ppt. removed by filtration and filtrate concd. in vac.; elem. anal.;	91%
With magnesium In tetrahydrofuran at 20℃; for 2.58333h; Inert atmosphere;	54%
With magnesium In tetrahydrofuran treatment of Mo(N(t-Bu)C6H3Me3)3 with excess 1,1-dichlopropane (2 equiv.) in the presence of Mg in THF at room temp.;

lithium aluminium + (4S,5S)-Dimethyl 2-(2-chlorophenyl)-1,3-dioxolane-4,5-dicarboxylate (102301-10-0) + 1,1-dichloropropane (78-99-9) → 2-O-(2-chlorobenzyl)-D-threitol (102301-11-1)

Conditions	Yield
With sodium hydroxide; aluminium trichloride In dichloro-1-propanol; water	81%

1,1-dichloropropane (78-99-9) + thiophenol (108-98-5) → 1,1-bis(phenylthio)propane (15486-58-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 150℃; for 0.333333h; microwave irradiation;	79%

1,1-dichloropropane (78-99-9) + cannabidiolic acid (1244-58-2) → 2-ethyl-7-hydroxy-8-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl)-5-pentyl-4H-benzo[d][1,3]dioxin-4-one

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 130℃; for 4h; Sealed tube;	23%

tetrahydrocannabinolic acid (23978-85-0) + 1,1-dichloropropane (78-99-9) → (8aR,12aR)-2-ethyl-8,8,11-trimethyl-5-pentyl-8a,9,10,12a-tetrahydro-4H,8H-benzo[c][1,3]dioxino[4,5-f]chromen-4-one

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 130℃; for 4h; Sealed tube;	7%

1,2-Dichloropropane (26198-63-0, 78-87-5) + 2,2-dichloropropane (594-20-7) + 1,1-dichloropropane (78-99-9) → octachloropropane (594-90-1)

Conditions	Yield
durch Einleiten von Chlor unter Belichtung und allmaehlicher Erhoehung der Reaktionstemperatur auf 200grad;

1,1-dichloropropane (78-99-9) → propane (74-98-6)

Conditions	Yield
With alkali metalammonium; ammonia

1,1-dichloropropane (78-99-9) → propylidene difluoride (430-61-5)

Conditions	Yield
With hydrogen fluoride; mercury(II) oxide
With pyridine; hydrogen fluoride; mercury(II) oxide

1,1-dichloropropane (78-99-9) → 1-chloro-1-fluoro-propane (430-55-7)

Conditions	Yield
With hydrogen fluoride; mercury(II) oxide

1,1-dichloropropane (78-99-9) → 1,1,2-trichloropropane (598-77-6)

Conditions	Yield
With chlorine im Sonnenlichte;
With chlorine
With antimonypentachloride

1,1-dichloropropane (78-99-9) → propenyl chloride (590-21-6)

Conditions	Yield
at 100℃; alkoh.Kali;

1,1-dichloropropane (78-99-9) → 1-bromo-2,2-dichloropropane (85925-71-9)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 15℃; Irradiation; competition reaction with neopentane and tert-butyl chloride; relative rate constants for mediated brominations; additives - Br2, CH2CCl2, BrCCl3;

1,1-dichloropropane (78-99-9) → trans-1-Chloropropen (16136-85-9) + 1,2-Dichloropropane (26198-63-0, 78-87-5) + cis-1-chloropropene (16136-84-8) + 3-chloroprop-1-ene (107-05-1)

Conditions	Yield
With potassium chloride; sodium chloride; zinc(II) chloride at 400℃; for 0.5h; Product distribution; other gem-dichloroalkanes; var. molten salt catalysts; var. temps.;	A 8.8 % Chromat. B 12.8 % Chromat. C 19.4 % Chromat. D 3.0 % Chromat.

1,4-dioxaspiro[4.4]non-6-ene (695-56-7) + 1,1-dichloropropane (78-99-9) → 6-Chlor-6-ethylbicyclo<3.1.0>hexan-2-on-ethylenacetal

Conditions	Yield
With n-butyllithium In hexane; pentane 1.) -40 - -30 deg C; 2.) -30 deg C to -10 deg C, 3 h;	1.06 g

1,1-dichloropropane (78-99-9) + water (7732-18-5) + iron → hydrogenchloride (7647-01-0)

Conditions	Yield
Geschwindigkeit;

1,1-dichloropropane (78-99-9) + NaHCO3 → hydrogenchloride (7647-01-0)

Conditions	Yield
Geschwindigkeit;

1,1-dichloropropane (78-99-9) + ammonia (7664-41-7) + alkali metalammonium → propane (74-98-6)

1,1-dichloropropane (78-99-9) + hydrogen fluoride (7664-39-3) + mercury (II)-oxide → propylidene difluoride (430-61-5)

1,1-dichloropropane (78-99-9) + hydrogen fluoride (7664-39-3) + mercury (II)-oxide → 1-chloro-1-fluoro-propane (430-55-7)

Upstream product

• 74-98-6 propane 
• 123-38-6 propionaldehyde 
• 590-21-6 propenyl chloride 
• 75-27-4 bromodichloromethane 
• 74-85-1 ethene 
• 540-54-5 1-Chloropropane 
• 7782-50-5 chlorine 
• 78-00-2 tetraethyllead(IV) 

Downstream Products

• 74-98-6 propane 
• 430-61-5 1,1-difluoropropane 
• 430-55-7 1-chloro-1-fluoro-propane 
• 26198-63-0 1,2-Dichloropropane 
• 592-42-7 1,5-Hexadien 
• 590-21-6 propenyl chloride 
• 107-05-1 3-chloroprop-1-ene 
• 102301-11-1 2-O-(2-chlorobenzyl)-D-threitol 
• 220628-21-7 Ru(H)Cl(N₂)(P(C₆H₁₁)3)2 
• 3384-04-1 3-chloropropyl phenyl ether 
• 15486-58-5 1,1-bis(phenylthio)propane 
• 7647-01-0 hydrogenchloride 
• 598-77-6 1,1,2-trichloropropane 
• 16136-85-9 trans-1-Chloropropen 

Relevant articles and documents

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THE LONG-RANGE ACTION OF THE POLAR EFFECT OF SUBSTITUENTS ON THE ABSTRACTION OF HYDROGEN IN FREE-RADICAL CHLORINATION PROCESSES

The free-radical chlorination of 1-chloroalkanes between C3 and C6 at 263 deg K was studied under conditions with wide variation in the concentrations of the substrates in benzene.By analysis of the products from chlorination of the pure substrates it was shown that the deactivating effect of the polar substituent does not extend beyond the third carbon atom and is mainly determined by the inductive effect.In the transition to an aromatic solvent the deactivating effect on the substituent extends to the fourth carbon atom.The results are substantiated in terms of a contribution from dipole-dipole interaction between the substituent and the polar form of the transition state to the polar effect of the substituents.